The mass spectral rearrangements of aryl propenyl sulfones. An electron impact induced smiles type rearrangement

The mass spectral behavior of trans‐1‐arylsulfonyl‐2‐arylsulfenyl‐propenes, trans‐1‐arylsulfonyl‐2‐arylsulfinyl‐propenes and trans‐1, 2‐(arylsulfonyl)‐propenes was examined. A Smiles type rearrangement was present in the sulfonyl‐sulfides, but was completely absent in the trans‐1‐arylsulfonyl‐2‐arylsulfinyl‐propenes and trans‐1, 2‐(arylsulfonyl)‐propenes. Vinyl migration to the sulfone oxygen predominates over aryl migration in all of the compounds studied. The mass spectra of the cis and trans isomers of 1‐p‐tolylsulfenyl‐2‐p′‐tolysulfonyl‐propene and 1, 2‐(p‐tolylsulfonyl)‐propene are also described.